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| 4/29/2023 | Charleston Speedway - Charleston, IL 60th Annual Season Opener! +6 Divisions of Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 4th | - | - | 5th |
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| 5/6/2023 | Spoon River Speedway - Canton, IL IMRA at Spoon River Speedway Limited Modified: HART Limited Modified Series Midgets, DIRTcar UMP Modifieds, DIRTcar Pro Late Models, DIRTcar 4 Cylinders | Results | | Josh Jackson (DIRTcar Pro Late Models) | 4th | - | - | 5th |
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| 5/27/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 3rd | - | - | 3rd |
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| 6/3/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 3rd | - | - | 2nd |
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| 6/10/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 5th | - | - | 3rd |
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| 6/17/2023 | Charleston Speedway - Charleston, IL Father's Day Special + Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 2nd | - | - | 3rd |
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| 6/24/2023 | Charleston Speedway - Charleston, IL Summer Shootout Double Points Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 3rd | - | - | 8th |
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| 7/15/2023 | Charleston Speedway - Charleston, IL The 38 Special for DIRTcar Modified presented by Leaf Tree Service. DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 3rd | - | - | 6th |
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| 7/22/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 4th | - | - | 5th |
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| 8/5/2023 | Charleston Speedway - Charleston, IL Fan Appreciation Night + Driver Autographs + Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Josh Jackson (Dirt Late Models) | 7th | - | - | DNS |
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